Regioselective Asao-Yamamoto benzannulations of diaryl acetylenes

Hasan Arslan, Katherine L. Walker, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Asao-Yamamoto benzannulations transform diarylalkynes into 2,3-diarylnaphthalenes, and regioselective variants of this reaction are of interest for synthesizing substituted polycyclic aromatic systems. It is shown that regioselective cycloadditions occur when one alkyne carbon preferentially stabilizes developing positive charge. Simple calculations of the relative energies of carbocations localized at each alkyne carbon of a substrate predict the regioselectivity, which is not eroded by bulky substituents, including 2,6-disubstituted aryl groups.

Original languageEnglish (US)
Pages (from-to)5926-5929
Number of pages4
JournalOrganic Letters
Volume16
Issue number22
DOIs
StatePublished - Nov 21 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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